
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $203 (FlightHub) |
One-way from | $125 (iWofly) |
Popular in | July |
Cheapest in | November |
Average price | $294 |
Good round-trip deal | $190 or less |
Good one-way deal | $94 or less |
Fly from
Fly to
Route
Depart
Return
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Fri 9/11
1:40 pm-2:35 pm
Nonstop1h 55m
Chicago O'Hare Intl
Sun 9/13
11:45 am-2:25 pm
Nonstop1h 40m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 5/22
8:50 am-9:50 am
Nonstop2h 00m
Chicago O'Hare Intl
Wed 5/27
7:09 am-9:54 am
Nonstop1h 45m
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Mon 6/15
7:20 pm-8:16 pm
Nonstop1h 56m
Chicago O'Hare Intl
Thu 6/18
7:25 am-10:06 am
Nonstop1h 41m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 6/2
12:09 pm-4:29 pm
1 stop5h 20m
Chicago O'Hare Intl
Wed 6/3
5:19 pm-10:59 pm
1 stop4h 40m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 6/19
7:43 pm-11:26 pm
1 stop4h 43m
Chicago O'Hare Intl
Mon 6/22
9:20 pm-11:59 pm
Nonstop1h 39m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 6/6
12:09 pm-4:29 pm
1 stop5h 20m
Chicago O'Hare Intl
Tue 6/9
7:01 am-11:19 am
1 stop3h 18m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 6/18
2:29 pm-6:29 pm
1 stop5h 00m
Chicago O'Hare Intl
Sun 6/21
7:01 am-3:19 pm
1 stop7h 18m
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Wed 9/23
8:40 pm-9:35 pm
Nonstop1h 55m
Chicago O'Hare Intl
Sun 9/27
11:45 am-2:25 pm
Nonstop1h 40m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 7/20
10:15 am-11:21 am
Nonstop2h 06m
Chicago O'Hare Intl
Thu 7/23
7:09 am-9:54 am
Nonstop1h 45m
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Sat 6/20
12:15 pm-1:10 pm
Nonstop1h 55m
Chicago O'Hare Intl
Sun 6/28
7:25 am-10:06 am
Nonstop1h 41m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
The best time to book flights from Toronto to Chicago O'Hare Intl Airport is 90 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago O'Hare Intl Airport (average of $51). Flying from Toronto to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $158). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
When flying from Toronto to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 44% versus a flight in the afternoon.
Travelers seeking maximum savings on their Toronto to Chicago O'Hare Intl Airport flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from YTO to ORD are scheduled on a Monday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 on average).
Montreal (YUL) – chosen by Cheapflights users on 50% of 1-stop itineraries from Toronto to Chicago O'Hare Intl Airport on Cheapflights.
Detroit (DTW) is the most affordable 1-stop option, with an average round-trip price of $260.
Flights via Detroit (DTW) have the shortest average one-way travel time for 1-stop routes: 3h 14m.
Flights via Detroit (DTW) offer the fastest connection on this route, with an average layover time of 1h 24m.
About 12% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 140 minutes.
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Thursday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 8% of flights being delayed.
Boarding
Crew
Entertainment
Overall
Food
Comfort
Reviews
Anonymous,Oct 2025
YUL - ORD
Boarding
Crew
Entertainment
Overall
Food
Comfort
Reviews
Anonymous,Oct 2025
YUL - ORD
Boarding
Crew
Entertainment
Overall
Food
Comfort
Reviews
Anonymous,Oct 2025
YUL - ORD
Boarding
Crew
Entertainment
Overall
Food
Comfort
Reviews
Anonymous,Oct 2025
YUL - ORD
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$146 | Average$281 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$165 | Average$269 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$286 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$192 | Average$411 | FlexibilityNo cancel fee | On-time52% |